The More Things Change, the More They Stay the Same
by Gronzen
Summary: His curse wasn't as simple as being Undead, destined to Hollow. It the curse of the Dark Soul, of carrying Manus' power. Even here, in this land beyond Lordran and its time, it haunted him. At least he still had his allies here. Kind of...
1. Chapter 1

**Disclaimer**

 **High School DxD is owned by Ichiei Ishibumi / Funimation**

 **Dark Souls is owned by FromSoftware**

* * *

Issei sat with his back against the wall, breathing heavily.

' _Damn it… I'm not going to make it out of this one, am I?'_

"Where did he go!?"

' _I can't run anymore. My body is too messed up at this point…'_

"There he is!"

' _My only regret…'_

"Time to die!"

'… _is that I didn't see their more of their boobs.'_

"This is what you getting for peeping on the soccer team, pervert!"

He watched as the captain of Kuoh Academy's soccer team bounced her ball on her knee, and knew her chest was mocking him as it bounced as well. He was so close, but of course Matsuda and Motohama had to hog the peephole. Their arguing got the girl's attention real quick, and they wasted no time in dispensing justice to the trio. The other two had managed to get away but Issei was not so lucky. Issei closed his eyes and awaited the inevitable.

 **BWAK!**

"…What the hell!? Who're you!?"

Issei opened his eyes to see someone standing in front of him. Blue shirt, jeans, and… purple hair? He could see they had both arms up in front of their face. By their foot was the weapon of his execution.

"What, are you one of those perverts too?" Their captain accused, but the stranger just stooped down and picked up their ball. He tossed it back to them, and the captain stared at them for a moment before sticking her nose into the air.

"Hmph! Let's go girls. I think the pervert learned his lesson." With that the soccer club turned their backs on them and left. Issei's savior watched them for a moment before leaving.

"Hey, wait!" Issei stood, using the wall for support, "Who are you?"

They didn't answer, and as they walked off Issei nodded to himself.

' _I don't know who you are, but I'll never forget this!'_

* * *

' _It would seem you're a troublemaker even here, old friend. I suppose I'll have to help you as I did then…'_

* * *

Issei sighed in relief as he sat down at his desk. He had just managed to avoid the soccer club on the way here. He knew better than to hope they had already forgotten about yesterday.

"Attention, everyone, attention." The teacher clapped his hands, and everyone went quiet, "We have a new student joining us today."

The door slid open, and everyone began whispering. A boy with purple hair tied back in a ponytail, piercing, emerald eyes, and a small frown on their face. He bowed at the waist.

"Hello. I am Gwynnus Cindre. It is a pleasure to meet you all." His voice was quiet and formal, and the girls started whispering. Issei, however, rubbed his eyes to make sure he was seeing the right thing.

' _Purple hair? Then, is he…?'_

Gwynnus stood back up, looked over at Issei and nodded. The girls all gasped dramatically.

"Nooo! He's another pervert!"

"And he was so handsome, too!"

As the girls lamented, Issei gave a determined smile and nodded.

' _Don't worry, Gwynnus. Perverts stick together!'_

* * *

' _Hmm… It would appear you've changed more than expected…'_

* * *

"Gwynnus Cindre, age 15, adopted son of Gwyn Cindre." Sona pushed her glasses up, watching the purple-haired boy from the roof, "Top of his class in his previous schools…"

"…and a human covered in more darkness than a high-class devil." Rias tucked a lock of hair behind her ear, "Cindre… I've heard that name before…"

Sona nodded, "Currently, Gwyn Cindre, head of the family, controls most of the jewelry businesses in town. If it's made of gold or silver, it's most likely from one of his stores. There's also a rumor that he disowned one of his sons, going so far as to destroy every record of his existence."

Rias frowned when she heard that, "What could he have possibly done?"

"If I recall, the rumor said his son aided a rival, though it's unclear whether that means another business or a specific person. I'll do more research into the Cindre family…"

"…And _I_ will keep an eye on Gwynnus." Rias' blue eyes glared into a pair of emerald eyes…

* * *

Gwynnus turned back to his notebook, ignoring the two girls glaring at him from the rooftop. While he wasn't quite as strong as he used to be, he should still be able to handle them.

Soon enough lunch came, and as Gwynnus was heading for the door he felt a hand on his shoulder. He turned around to see Issei and two others looking seriously at him.

"Follow us."

He only nodded, and as they led him outside he pulled out a cloth hidden in his sleeve. They reached their destination and when they turned around they stared at each other for a moment.

"Alright, Gwynnus. I have only one question for you…"

The tension was thick enough to cut with a blade, and as Gwynnus could only wonder what question could earn such gravity.

"…Boobs, or butts?"

'… _Did… did he just ask…?'_

"I… don't understand the question…"

"What's there to understand!? Are you a boob man or an ass man!?" Issei and his friends were suddenly much closer than he preferred. He felt his cheeks flush as he tried to come up with an answer.

"I, t-that is to say-"

"Excuse me."

Gwynnus turned around to see a blonde haired boy smiling at them, a crowd of girls following shortly behind.

"I am Kiba Yuuto of the Occult Research Club. You are Gwynnus Cindre, correct?" At Gwynnus' nod he continued, "I was asked by our president, Rias Gremory, to invite you for tea after school."

Everyone burst into conversation at that, Issei and his friends exclaiming jealousy for this opportunity, the girls praising Kiba for getting him away from the 'Perverted Trio'.

Both sides joined in shock when Gwynnus shook his head.

"My apologies, but I am kept to a strict schedule. Perhaps I can convince my father to allow me some time after school."

Kiba's smile became a bit strained, "Of course. See you another time, then."

With that, he and his entourage walked off as the bell rung. Gwynnus started walking back to class, a mixture of dread and numbness taking over as Issei started walking with him.

' _Please, please don't make me fight you again, brother…'_

* * *

" _HYAAARGH!"_

 _The foolish abomination tilted its body up to stare at him, allowing him to safely land on it and crush it beneath his weight. He felt a weight land on his back, and a moment later his comrade leapt onto the beast in front of him, skewering it. As it fell, the blue garbed warrior leapt off, two tentacles reaching for him. He brought his zweihander down, severing the appendages, and the creature screeched as his comrade turned and loosed a great ball of flame upon it. Another approached from his right and he charged it. It rose up to stomp upon him, but he went into a slide, and as he slid under it he brought his sword up._

 _He stood and turned when his slide finished, smiling as the creature's innards fell and it collapsed. He looked towards his companion, his smile unseen. As he was about to congratulate him, he saw one last beast rushing him from the darkness. He couldn't reach him in time… unless…_

" _Get down!"_

 _He hurled his blade as hard as he could, and it soared true. His friend ducked and the beast was pinned to the wall. His smile grew, even as the adrenaline wore off and he fell onto his rear. He waved off the attempt to help him up._

" _Don't worry about me. Just a quick rest, and I'll be off again."_

 _He could feel the worried look, but his friend nodded and set off. He laughed when their footsteps died out. Finally, he was the hero he_ _ **knew**_ _he could be. He slowly closed his eyes, and a strange bliss took over him…_

* * *

Issei quickly sat up, blinking the sweat from his eyes.

"What the hell was that dream?"

He looked around his bedroom, taking note of how the sun was just rising. He yawned before lying back in bed. He had a few minutes before he had to get ready for school.

He shot back up, a great realization overtaking him.

"Gwynnus never said whether he liked boobs or not!"

* * *

 **AN: I couldn't think of anything else that fit with the 'Gwyn' naming scheme, so Gwynnus it is. To be clear, this will be a Dark Souls 1 only story.**


	2. Chapter 2

**Disclaimer**

 **High School DxD is owned by Ichiei Ishibumi / Funimation**

 **Dark Souls is owned by FromSoftware**

* * *

 _He breathed heavily as he slumped against the cave wall. He knew he didn't outrun his pursuers, but he was too exhausted to run anymore. He heard three sets of hoof falls, and then the creaking of armor. Three knights strode into view, an overreaction in his opinion. They said nothing, merely grabbing him and hauling him outside. One of the horses was hooked to a caged carriage, and he quickly found himself tossed inside._

 _One of the knights, the leader, he assumed, stared at him for a long moment before speaking, "May I never see you again, beast."_

* * *

Gwynnus' eyes snapped open, his heart racing. Taking a look around his room and confirming he was still at home, he sighed. He took a moment to make sure his heart was calmed, and looked towards his clock. Six a.m. on the dot, meaning it was time for him to get up. He did the typical morning routine, dressing in his school uniform afterwards. He opened his door and made his way through the grand hallways to the dining room.

The servants along the way gave the usual curt 'young master' as they bowed to him. Eventually he reached the long table where his family usually ate. It was enough to seat at least twenty-six people, but at the moment served only four.

His older sister, Gwynevere, was sitting to the left of the table head. Her reddish hair curled around her shoulder, her white blouse straining against her chest. Next to her was Gwyndolin, dress in a long-sleeved white shirt. Behind him ( _her_ , he reminded himself) was their ever present guard, clad in her usual business suit and face wrapped in bandages. Normally, they would be greeting him with a smile, but their faces were carefully neutral. When he saw who was occupying the table head, he understood why.

He bowed at the waist, "Mr. Cindre."

The man at the head of table would never tolerate Gwynnus referring to him as 'father'.

Gwyn Cindre had made it _very_ clear: he was not his son. He was a guest invited into his home by his daughters.

"Rise." Was his simple reply, and Gwynnus did so. He walked past the man, sitting at a much smaller table in the corner of the room. The main table was reserved for those of the family or important guests, after all. A maid brought out toast and butter, and gave only a shallow bow before leaving. Breakfast was held in silence, and when he was finished he brought his plate to the kitchen before heading to school…

* * *

The day went on fairly normally once he reached school. Classes were what one would expect, though lunch was something of an issue…

"What… _are_ these?" There was a stack of magazines on the ground between him and the 'Perverted Trio'. The top one had a woman with _very_ little clothing in a _very_ risqué position on the cover.

"These are gonna help you decide on boobs or butts!" Issei smiled, his friends nodding beside him.

' _Oh Flames take me now…'_

"Issei, I, don't feel comfortable talking about this, and at _school_ of all places."

To his surprise Issei nodded, "It's alright Gwynnus, I understand."

'… _He's going to say something strange, isn't he?'_

"We can look them over at my place! I have plenty for you to take home, too!"

'… _How is he more ridiculous_ _ **now**_ _than before!?'_

"Pardon the intrusion gentlemen." They turned around to see Kiba, who was staring straight at Gwynnus, "So, were you able to convince your father?"

"…No, I was not."

"Oh? That's a shame."

"Actually, it's probably for the best. I'm not really comfortable dealing with a large group."

Kiba smiled sadly, "Sometimes, these things are not meant to be. Well. I'll leave you to your… _business_ , then." With that the blond walked off, and when he disappeared Gwynnus hummed.

"That was… odd. He gave up rather quickly."

"Don't tell me you actually _want_ to hang out with that pretty boy bastard!?" Issei shouted, and he turned back to see his shocked face with the other two nodding.

"Why? He doesn't seem so bad."

"Not so bad!? He hoards all the girls to himself, lording them over us! We have to risk life and limb just to see the briefest flash of boob while he has his pick of the litter! All because he looks good! If we-" Issei blinked, then stared hard at Gwynnus.

"…What?'

"That's it!" Issei's smile practically split his face, "You can show us boobs!"

"…WHAT!?" Was the simultaneous shout by Gwynnus and the others.

"What the hell, man!? I know we're desperate but we're not that desperate!" Matsuda shouted.

"Look, we're practically sitting on a gold mine here!" Issei shouted back.

"I-I-I will do no such thing!" Gwynnus could feel his face burning, and he was suddenly very self-conscious about his appearance, "Even if you are a friend, I am not doing _that_!"

"Please, Gwynnus! This is our only chance at the biggest boobs in school!"

"…Eh?" It was all Gwynnus' brain could get out at this point.

"Think about it! If you join the Occult Research Club, then you'll be able to get close to the two Great Ladies of Kuoh! Then you lay on the pretty boy charm and with a spy camera from Motohama…" A disturbing look came over his face.

"Wait a minute, Koneko Toujou is part of the same club, isn't she!?" Motohama looked pleadingly at Gwynnus, "You gotta do it, man!"

"Akeno Himejima, 40-24-35. Rias Gremory, 39-23-35." Motohoma rattled off from memory.

Gwynnus shook his head, "I can't believe this."

"I know, great plan, right?" Issei beamed.

Gwynnus shook his head, "Issei… no."

"Eh? What's wrong with it?" Issei tilted his head, and Gwynnus stared at him for a moment.

"…You really don't know, do you?" He sighed, and turned away from them, "I'm going back to class."

"Wait, what about the magazines!? We need to know-"

Issei's voice trailed off as Gwynnus walked away…

* * *

He avoided the trio for the rest of the day, and he found himself lost in his thoughts on his way home. How could Issei be so… different? He passed into the park, eventually sighing and sitting at the edge of the fountain.

'… _Of course he's different.'_ Gwynnus ran a hand on the fountain's rim, _'Everything,_ _ **everyone**_ _is different. Issei, my sisters, even… even me. If-'_

The air suddenly felt charged, and he felt old instincts kick in as he leapt away from the fountain. There was a crash, and he looked back to see a blue spear embedded where he was sitting. Black feathers fell from above, and he looked up to see a man in a trench coat and fedora looking down at him. He hovered in the air with two black-feathered wings, and the two stared each other down.

"Aren't you an interesting one? A little Devil with a gift from the Heavens?"

"I am no Devil!" Gwynnus shouted, and the man laughed harshly.

"You truly think I would believe that?" A blue spear appeared in his hands, "I slayed enough of your kind to know your stink by now. Any last words?"

Gwynnus kneeled, and he slipped the cloth hidden in his sleeve into his hand before he clasped his hands together.

"You truly believe God would listen to the prayers of one of your ilk?" The mam sneered, and he threw the spear-

"Force."

A white shockwave knocked the end over end back towards the man, who only looked shocked for a moment before he dodged out of the weapon's way. Gwynnus' left hand burst into flame, and he slammed it into the ground. Pillars of flame rose all around him, and when they died down he saw the man clutching his burnt right arm and burnt wing close to his body. He started circling the man, and the man conjured a spear in his good hand.

"Damn you!" He threw the spear, but it passed by Gwynnus without issue. In return he sent a Chaos Fireball, and the man disappeared in a flash. After a moment he felt the rush of soul energy, and he walked up to where the fireball landed. The lava had cooled into black, lumped stone, no physical trace of the man remaining.

Instead, a warm, flickering light proved the man once stood there.

The soul was a strange thing, bright, but with dark streaks appearing and disappearing throughout it. As he reached for it, it seemed to almost recoil, and it began releasing sparks of energy when he grasped it. He studied it for a moment longer before crushing it, and he felt the power rush into him. With one last look around he opened his schoolbag…

* * *

Issei smiled as he and his new girlfriend walked through the park. He had to admit, it was a shock that a girl would approach _him_ , but he wouldn't complain! He was brought out of his thoughts for a moment when he felt Yuuma's hand slip into his own.

"Issei, I had a really nice time today." She smiled at him, and he could swear he felt his heart stop. The sun shone against her long black hair, her red eyes like rubies, and her chest shifted with each breath.

"Me too." Issei smiled, and he congratulated himself for not blowing this chance.

She looked ahead, "I have a… a…" her smile disappeared, and she blinked in confusion, "What?"

"What?" Issei followed her gaze, and he saw something glowing near a wrecked fountain. They approached the fountain, and Issei saw that there was something written in English on the ground.

"What the heck happened here?" Issei looked around the ruined area.

"Huh, it says 'be wary of ambush'. How fitting."

Issei blinked in confusion as he heard Yuuma's voice behind him, "Wait, why is that fitting?"

* * *

Gwynnus quietly entered the Cindre household and made his way up to his room. To his surprise both his sister were there, Gwyndolin in his desk chair and Gwynevere lying on his bed.

"Hello brother." Gwyndolin said softly.

"Brother dearest." Gwynevere nodded towards him.

He felt a smile form for a moment before it dropped, "Sisters, I have an important question."

They gave him concerned looks, and he continued.

"Do I look like a girl?"

* * *

 **AN:** **Not much plot, just establishing some things and transition. I would've liked to have made it longer, but I just don't have the patience or the energy atm. Also f*ck Patches… That had nothing to do with the story, just wanted to say it.**


	3. Chapter 3

**Disclaimer**

 **High School DxD is owned by Ichiei Ishibumi / Funimation**

 **Dark Souls is owned by FromSoftware**

* * *

Gwynnus tried to take down notes as his teacher spoke, but his mind was more than a bit pre-occupied. His sisters had avoided his question yesterday, not to mention the being he encountered still plagued his thoughts. He knew better than to hope that it was just a random encounter. The powers that be would take notice of him now.

Another 'quest' that he wanted no part of.

He shook away the dark thoughts straying into his mind. He would deal with that another day. For now, he had to plan for tomorrow…

* * *

She breathed lightly, the usual pain that wracked her down to a dull throb. She was always grateful for the medicine the doctors gave her. She knew it wouldn't truly bring back her old life, but she had Eingyi, and her sisters. Oh, and Kirk, and that nice boy that visited her on Sundays. They were always trying to make her feel better-

"My Lady, you have a guest."

She smiled, and in her mind she could see Eingyi's old, withered smile. She felt movement by her side, and a hand gently grasped her own.

"Hello, Gwynnus." She whispered, and he laughed lightly, "I'm surprised you're here on a Thursday."

"You always seem to know it's me."

"Of course. You're my friend."

"…Right. How… how has everyone been?"

"Our esteemed sister," Quelaana's voice was heavy with sarcasm, and she could _feel_ her red eyes glaring out from beneath her black-and-gold shawl, "has been too busy to visit."

"Quelaana, you know she would visit more. She said she may have found a way to cure me, did she not?" Her sister said nothing for a moment before sighing.

"We both know there is none." She felt Gwynnus' hand tense, and the air grew heavy, "We _all_ know it."

"…That does not mean she doesn't care. Someone must manage the estate." Her voice was even quieter. It… it was the truth. Quelaag was the heir, as Quelaana had given up her right to inheritance and she was…

The door opened, and the silence was broken by a harsh voice, "Why are **you** here?"

"Sister-" she started, but she felt Gwynnus' hand leave her own.

"Visiting."

"You've visited. Leave."

He did so, and after a moment she felt Quelaag loom over her.

"You know I do not trust him."

She wanted to say 'but you don't trust anyone', but she knew better.

"You don't trust anyone."

Quelaana did not know better, apparently.

"With good reason," she growled, "how many have tried to take advantage of us already?"

"He isn't like that." It was true. He was the son of one mother's friends, and he'd proven himself to be a good person.

Quelaag went silent, but she knew it was more because she knew she'd already made up her mind and not because she was right.

"…I found another treatment for you."

She smiled weakly. This wouldn't be the first she heard those words, but who knows? Maybe this would be the one…

* * *

The next day, Issei returned to class, looking a little shaken. Gwynnus felt a bit bad that he hadn't noticed the boy's absence, but he was still upset at the time over the 'incident'. Also, something else was bothering him…

"Are you alright?"

Gwynnus blinked, "I could be asking you the same thing, Issei. Where were you yesterday?"

"Oh, uh, I was just a bit sick!" Issei laughed nervously, and Gwynnus decided not to pry. The day proceeded fairly normally, but the strange feeling never went away. He was on his way home now, walking along a side route he used sometimes.

' _What is it? I've felt this before, but what-'_

Something grabbed his shoulder, and he was thrown into an alley. He collided with the edge of a dumpster, and when he hit the ground he saw a woman in rags coming at him with a meat cleaver. He stood, his pyromancy flame coming to life, but not before she sunk the cleaver into his left arm. With a growl he placed his hand on her chest and she was sent flying back. A stream of fire flew from his hands after that, but she didn't even scream as the fire engulfed her and she collapsed. He pulled out the cloth he kept in his sleeve.

"Heal."

The gash in his arm shrunk, but there was still a noticeable cut. He tied the cloth to the wound and took out his cellphone, quickly dialing Quelaana's number.

' _Damn it, pick up!'_ He looked at the body, which was starting to dissipate, _'If_ _ **she's**_ _here then-'_

"Hello?"

"It's Gwynnus. Is… everything alright?"

"Yes, why? Has something happened?"

He sighed, "No, no, just worried."

"Hm, hm, hm, careful, one might think you care for us more friends."

He breathed out a laugh, "Please don't say that to your sister. I'd rather not give her more of a reason to want my head…"

They chatted for a short bit before he made his way home, bandaged his wound, and fell into sweet sleep…

* * *

' _Why did I ask what a cup size was?'_

It was an honest mistake. His sister had never referred to her bra size as 'cups', so when Issei had asked him what cup size he preferred, he had asked for a clarification.

Mistakes were made.

"And this," he gestured to the woman on the page, "is a double 'D'. Now, here we have-"

' _Regrets. Sooo many regrets.'_

"Excuse me," he turned to see Kiba, "I know you four are busy, but could I borrow Issei for a moment?"

The blonde walked Issei off, and Gwynnus turned to the remaining perverts…

* * *

"I do believe Rias' exact words were 'Avoid Gwynnus until I say otherwise'."

Issei frowned, "I know that, but Gwynnus is my friend, not to mention he saved my life! I can't just ignore him! Anyways, didn't Rias say he was a Devil too? What if I wind up recruiting him into the peerage?"

"It's not that simple, Issei. We don't know for certain if-"

"OKAYI'MDONEHEREBYE!"

Gwynnus sprinted past them, and they both blinked.

"What was that about?"

"I don't know. All we were doing was teaching him about cup sizes…"

* * *

She panted as she slumped against the wall. She was safe enough for now. What was that… what the hell _was_ that!? Gwynnus… did he know? Is that why he called earlier, to warn her?

"Damn it…" A flame came to life in her hand, and a reddish-pink ball of light flew from her fingertips. The message for help was clear, and when this was all over he was going to _damn well_ give her an explanation!

* * *

 **AN** **: The pyromancy Quelaana used was Undead Rapport. Which in DxD land is just Rapport, I guess. I'll explain it later.**


End file.
